Defensive publication

ABSTRACT

NOVEL DYES OF THE CARBOCYANINE, DICARBOCYANINE, MEROCYANINE AND MERCOCARBOCYANINE CLASSES DERIVED FROM IMIDAZOLIUM SALTS ARE USED TO ADVANTAGE AS SPECTRAL SENSITIZING DYES FOR PHOTOGRAPHIC SILVER HALIDE EMULSIONS. OUR SYMMETRICAL CARBOCYANINES AND DICARBOCYANINES ARE ADVANTAGEOUSLY PREPARED FOR CONDENSING ONE OF OUR IMIDAZOLIUM SALTS WITH AN APPROPRIATE INTERMEDIATE, SUCH AS, DIETHOXYMETHYL ACETATE, ETHYL ORTHOFORMATE, ETHYL ORTHOACETATE, ETHYL ORTHOPROPIONATE, TRIMETHOXYPROPENE, B-ANILINOACROLEIN ANIL HYDROCHLORIDE; OUR UNSYMMETRICAL CARBOCYANINES AND DICARBOCYANINE DYES IS ADVANTAGEOUSLY PREPARED BY CONDENSING OUR IMIDAZONUM ITS WITH INTERMEDIATES HAVING ANY OF THE 5- TO 6-MEMBERED BASIC HETEROCYCLIC NUCLEI, E.G., A THIAZOLE, A BENZOTHIAZOLE, A NAPHTHOTHIAZOLE A THIANAPHTHENO-7&#39;&#39;,6&#39;&#39;,4,5-THIAZOLE, AN OXAZOLE, A BENZOXAZOLE, A NAPHTHOXAZOLE, A SELENAZOLE, A BEMZOSELENAZOLE, A NAPHTHOSELENAZOLE, A THIAZOLINE, A PYRIDINE, A QUINOLINE, AN ISOQUINOLINE, A 3,3-DIALKYLINDOLENINE, A BENZIMIDAZOLE, A NAPHTHIMIDAZOLE, ETC. USED IN CYANINE-TYPE DYE WHILE THE MEROCYANINE AND MEROCARBOCYANINE DYES ARE ADVANTAGEOUSLY PREPARED BY CONDENSING OUT IMIDAZOLIUM SALTS WITH ANY OF THE INTERMEDIATES CONTAINING 4TO 6-MEMBERS HETEROCYCLIC KETOMETHYLENE NUCLEI, E.G., A 3-THIETANONE-1,1-DIOXIDE, A 2-THIO-2,4-THIAZOLIDINEDIONE, A RHODANINE, A 2-THIOBARBITURIC ACID, A BARBITURIC ACID, A 2-THIOHYDANTOIN, A HYDANTOIN, A 2-THIO-2,4-OXAZOLIDINEDIONE, A 2-THIAZOLIN-4-ONE, A 2-PYRAZOLIN-5-ONE, A 2-IMID AZOLINE-4-ONE, A 2-IMIDAZOLIN-4-THIONE, A 2-IMIDAZOLIN-4SELENONE, ETC USED TO MAKE MEROCYANINE-TYPE DYES.

DEFENSIVE PUBLICATION UNITED STATES PATENT OFFICE Published at the request of the applicant or owner in accordance with the Notice of Dec. 16, 1969, 869 0.G. 687. The abstracts of Defensive Publication applications are identified by distinctly numbered series and are arranged chronologically. The heading of each abstract indicates the number of pages of specification, including claims and sheets of drawings contained in the application as originally filed. The files of these applications are available to the public for inspection and reproduction may be purchased for 30 cents a sheet.

Defensive Publication applications have not been examined as to the merits of alleged invention. The Patent Ofiice makes no assertion as to the novelty of the disclosed subject matter.

PUBLISHED FEBRUARY 2, 1971 T883 014 SILVER HALIDE EMUESIONS CONTAINING IMIDSAZOLIUM SPECTRAL SENSITIZING DYE Donald W. Hcseltine, 22 Edgewater Lane, and Leslie G. S.

Bugger, 915 Winona Blvd., both of Rochester, N.Y.

Filed June 1, 1970, Ser. No. 42,534 Int. Cl. G03c 1/08, 1/10 US. Cl. 96131 No Drawing. 27 Pages Specification Novel dyes of the carbocyanine, dicarbocyanine, merocyanine and merocarbocyanine classes derived from imidazolium salts are used to advantage as spectral sensitizing dyes for photographic silver halide emulsions. Our symmetrical carbocyanines and dicarbocyanines are advantageously prepared by condensing one of our imidazolium salts with an appropriate intermediate, such as, diethoxynrethyl acetate, ethyl orthoformate, ethyl orthoacetate, ethyl orthopropionate, trimethoxypropene, [i-anilinoacrolein anil hydrochloride; our unsymmetrical carbocyanines and dicarbocyanine dyes are advantageously prepared by condensing our imidazolium salts with intermediates having any of the 5- to 6-membered basic heterocyclic nuclei, e.g., a thiazole, a benzothiazole, a naphthothiazole, a thianaphtheno-7,6,4,5-thiazole, an oxazole, a benzoxazole, a naphthoxazole, a selenazole, a benzoselenazole, a naphthoselenazole, a thiazoline, a pyridine, a quinoline, an isoquinoline, a 3,3-dialky1indolenine, a benzimidazole, a naphthimidazole, etc. used in cyanine-type dyes while the merocyanine and merocarbocyanine dyes are advantageously prepared by condensing our imidazolium salts With any of the intermediates containing 4- to 6-membered heterocyclic ketomethylene nuclei, e.g., a 3-thietanone-l,l-dioxide, a 2-thio-2,4-thiazolidinedione, a rhodanine, a Z-thiobarbituric acid, a barbituric acid, a Z-thiohydantoin, a hydantoin, a 2-thio-2,4-oxazolidinedione, a 2-thiazolin-4-one, a 2-pyrazolin-5-one, a Z-imid azolin-4-one, a 2-imidazolin-4-thione, a 2-imidazolin-4- selenone, etc used to make merocyanine-type dyes, 

